Sex, Money, and Serena Van der Woodsen
by spacebongo
Summary: What if Blair was the party animal and Chuck the straitlaced one? How different would Gossip Girl be then?
1. Chapter 1

**SEX, MONEY, AND SERENA VAN DER WOODSEN**

**BY SPACEBONGO**

_Sometimes Blair likes to imagine that had her father been alive he would have told her to try again, to keep trying until Nate eventually had no choice but to fall in love with her._

**What if Blair was the party animal and Chuck the straitlaced one? How different would Gossip Girl be then? This is not a straightforward 'personality transplant'. Blair is still Blair with her issues and hang-ups, and Chuck is still very much Chuck, and this is probably the worst summary ever so I shall shut up and let you read.**

**Warning: Underage, Mature, not really suitable for the squeamish.**

**-**

Blair always knew she wasn't good enough. Always knew that she would never keep a man happy how Eleanor Waldorf kept her late husband. And whenever she forgot Eleanor never flinched to tell her.

That is why she supposes she kissed Nate Archibald behind the swing set when she was six years old, to finally prove her mother wrong. But all Nate did was push her to the ground, wiped his lips with the back of a pudgy hand, and told her to keep her cooties to herself. Sometimes Blair likes to imagine that had her father been alive he would have told her to try again, to keep trying until Nate eventually had no choice but to fall in love with her.

But instead of trying again as she wanted to she just moved on to Carter Bazien who was older and handsomer and slipped her his tongue. After Carter she moved onto Jeremy Penarth who expected her to allow his hands to roam; then Daniel (Astoria not Humphrey because even if she was a pre-pubescent slut she wasn't desperate) followed by Trip Mathewson and by the time she returned to Carter Bazien in eighth grade there was very little she hadn't done in the janitor's closet.

Blair supposes she can blame losing her virginity to Carter Bazien's fingers on her mother, or the death of her father, or even Nate's cruel rejection of her in kindergarten. But she knows the truth. She was bored, full up with three bottles of the most expensive Dom money could buy, and absolutely shaking with rage because her best friend had finally gotten asked out by the one boy Blair had always been too afraid to approach.

Chuck Bass.

Chuck had always existed on the periphery of Blair's life. He was Nate's best friend, Serena's crush since kindergarten, Georgina's first kiss in the playground, Carter's first real arch nemesis; he was the heir of Bass Industries, popular, and hosted all of the best parties without ever getting embroiled in any of the scandals they created.

In short he was perfect and in love with Serena. And when they got together in eighth grade nobody was happier than Blair for her best friend.

"He's perfect for you," She had slurred as Serena helped wipe the blood from her thighs after Carter Bazien's less than gentle technique. "Rich, and sweet, and kind, and popular, and clearly still a virgin; but that's good." She touched a strand of Serena's golden hair as it curled from her fringe. "It means he'll try extra hard during your first time. Might even use his tongue." She stuck hers out and wiggled it suggestively until Serena blushed.

"You are such a slut," Serena laughed but it never reached her eyes and Blair rolled her eyes at the lecture she knew was coming. "Please don't do this again Blair. I can't bear seeing you hurt. Promise me."

"Okay," Blair promised seriously her eyes trying to focus on her beautiful friend. "I promise I won't ever lose my virginity again. You have my word, Serena. Want to pinkie swear?"

"I don't know why I bother," Serena threw bloodied toilet paper into the bowl and flushed. Then with a drawn out sigh she called her boyfriend. Her Chuck, the love of her God damned life, and asked him to bring out his limo for her as a 'personal favour'. Blair thought she was going to be sick at the sweet lilt of her best friend's voice and she was; all over Serena's brand new Jimmy Choo's.

-


	2. Chapter 2

**I have fleshed this story out now and think I know where it ends. However this part was difficult to write because I think the Chuck we saw in Seasons 1 and 2 without those outlets he enjoyed then would have been dangerous. I hope this conveys a little of that.**

**By the way, thank you so much for all of the supportive comments. I was a little surprised by all the positivity because I know the story's a little twisted, but please continue to let me know if this lives up to the first part. **

**- **

Blair only cared about three things. Money, insofar as it applied to her being able to buy as many shoes handbags and one-off couture pieces as she wanted, sex, and Serena Van der Woodsen. Blair cared so much about Serena in fact that sometimes it hurt just to even think about her. Like how it hurt to look at the sun, or how Blair imagined it hurt Chuck when Serena wasn't with him: sharp and aching with just a smidge of terror on the periphery to keep things interesting.

For instance the Friday before Blair's fifteenth birthday party when Chuck dragged them both to Tiffany's to buy the perfect necklace for Serena, her chest throbbed it was so painful. And it seemed to grow worse with every necklace that Chuck held up to Serena's swan like neck. Like that, with his hands on her shoulders as hers traced the delicate filigree of Tiffany's finest work against her throat, they looked like the most beautiful couple in the world. The thought, or perhaps the four Vodka Martinis she consumed over lunch, brought bile to her throat.

"I think this one is beautiful. What do you think Blair?" Serena's eyes snapped desperately to Blair's reflection in the mirror after each necklace. "Is it too much?"

"It's perfect," Chuck drawled his eyes burning from Serena to Blair. "Don't you think?"

Blair just smiled by way of reply. It kept them both happy and oblivious and focussed on each other rather than the lump in her throat or the tears that welled in her eyes from the pain of seeing Serena like that. Happy and glowing and with all of her hopes and dreams laid out like a golden path underneath her feet.

But the pain was at its worst a week later when Serena kissed Nate behind the stairwell between the boys' and girls' halls a minute before lunch. They clutched at each other desperately, her hands clawing underneath his white shirt, and his squeezing their way up under her skirt. The agony was so great that it almost knocked Blair off her game, almost stopped her from tearing off her clothes and streaking across the hall just in time to deflect the lunchtime scandal to herself. Of course she ran right into Chuck but the boy was nothing if not a gentleman and immediately bundled her up into his blazer.

"What is it now," He hissed as he frog marched her to his limo after that particular escapade. "Vodka, coke, heroin?"

And Blair supposed she deserved it; that cocktail of exasperation and disgust that always laced his words when she did something he didn't like. But she was a Waldorf. And if there was one thing that entailed it was the inability to take criticism from anybody, even the man of her best friend's dreams, even (especially) when she deserved it.

"And what do you care Bass? As long as your precious Serena wasn't involved," She spat out her best friend's name as he all but pushed her into his limo. "Don't think I don't know that the only reason why I'm here and not sitting in the Principal's office right now is because of my relationship to her."

"Blair…"

"You don't get to pretend you care about me." She tried to push his hands away when they cupped her face to get her to look at him, and she would have succeeded had she not been so surprised that he touched her at all. "Let me go." She whispered unconvincingly. "Please Chuck."

"Not until you tell me what you took," He drawled as he examined her eyes.

"Ten shots of Vodka," She blurted out just to stop feeling the heat of his fingertips on her skin. "Four of Scotch. And three blowjobs to three different guys in the space of thirty minutes." And because she was cruel, "But I could make it four if you're interested." She sidled up to him and fluttered her lashes. "I'm very good with my tongue, been told it could even raise the dead."

Chuck grimaced, disgust practically bleeding from his every pore, and snatched his hands from her almost like they had touched the most filthy thing in the world. And because Blair only cared about three things: sex, money, and Serena; she let him think the worst of her. Better her than Serena.

"Thanks but I'll pass," Chuck said smoothly after directing his driver to the Waldorf residence. "I prefer my girls STD free."

"And untouched from what I've heard," Blair spat out her best friend's deepest darkest secret (the one Serena had shared only when she was so drunk she couldn't even remember telling Blair the morning after) and Chuck's face drained of colour. "Don't worry your secret's safe with me. I mean who'd believe me? The great Bass heir, impotent. It's a wonder Serena isn't throwing herself at random guys _begging_ for it."

And possibly because she deserved it, or perhaps on account of the guilt of seeing Serena with Nate and not doing a thing to stop them, when the perfect Chuck Bass (the boy who would do anything to make his girlfriend smile) slapped Blair clean across his limo she took it with nothing more than a grimace.

"Don't tempt me," Chuck growled as he helped her up into the seat next to his with shaking hands and tears in his eyes, one hand clutched so tight around Blair's wrist that she had no choice but to lean up against him. "I'm not _that_ guy but I will break your fucking jaw if you say one more word."

And just like that the pain in Blair's chest, in her heart, intensified until she was unable to do much more than sit with her head pressed up tight against his chin. Chuck knew. About Serena. About Nate. He _knew_.

They spent the rest of the drive in silence.

-


	3. Chapter 3

**First of all thank you all so much for the amazing reviews so far. They have definitely motivated me to 'soldier on' in this story.**

**I am really not convinced with this part, even though it is the longest by far, which is why it took so long to write. I am trying to introduce my Blair and Chuck as characters as close to their canon characterisations as it is possible to get and still remain faithful with my reinterpretation of the story. But I think my Blair might still end up with more in common to canon Chuck than I am comfortable with. Please let me know what you think…**

**-**

Eleanor Waldorf was a woman of many faces and like any fashionista worth their salt she accessorised each impeccably according to the occasion. Her public face was that of the grieving widow who had sacrificed her youth to raise her only daughter; there she was softly spoken and kind and the ruthless gleam that normally sparkled in her eye was tampered by some kind of inner sweetness that must have been left over from when Harold Waldorf was alive. She only ever wore demure black dresses, her wild brown curls were tamed ruthlessly into a smooth chignon, and she wore her mid-heeled Kurt Geiger's proudly as though they could turn her to the Upper East Side's version of a soccer mom with just a click of the heels.

Blair knew the truth though. And as she downed champagne glass after glass at the muted soiree that Bart Bass threw for Eleanor Waldorf Designs in the same way she downed shot after shot of tequila with Serena during their non-Chuck approved trip to Tijuana the weekend of the Sheppard wedding, she wondered whether the socialites and business people that attended this function were aware of even the tiniest fraction of the cruelty her mother was capable of when it came to her only child.

"I would ask why you were intent on making a fool of your mother," Chuck Bass interrupted as she reached out for her tenth glass of champagne, intercepting and replacing it smoothly with a glass of orange juice. Freshly squeezed into an elegant wineglass, no ice, and decorated by thinly sliced Florida oranges and powdered brown sugar; it was perfect. "But I honestly don't care. Just don't make a fool of my dad. He worked too hard to set up this soiree for you to screw it up with your usual drunken antics."

"Somebody is feisty today," Blair turned up the corners of her mouth in a bitter smirk as she took another sip of her juice. "Well if you're looking for a fight Chuck then I'll have to ask you to find another opponent; I don't punch out of my weight class but I suppose you already knew that."

His jaw clenched hard like he had been slapped but he remained silent as his eyes burned furiously into the untouched glass of scotch in his hand. And Blair took the moment to look at him—brown hair combed neatly to the side, square jaw meticulously smooth, narrow shoulders and soft abdomen expertly dressed to exaggerate his leanness in a cream and gold three piece YSL suit that had not yet been shown even in Paris.

He looked good.

More than good, he looked tempting like those tall dark Eleanor Waldorf Designs models that Blair sometimes liked to take home two at a time to provoke a reaction from her mother. But Chuck was definitely not a harmless twenty year old grateful for any scraps of attention thrown his way by the first rich girl pretty enough to inspire an erection; he was cunning, and ruthless, and despite rarely playing those silly little power games that she and Serena sometimes did at school to make themselves feel more important when he did he played for keeps. Chuck was _Chuck Bass_ and he was _long term_.

That thought alone was enough to dry up any vestiges of attraction that she may have felt for him, because if there was one kind of man Blair Waldorf definitely did not do it was the kind she would be stuck with.

"I didn't mean to hurt you," Chuck said evenly after letting her stare at him for an inappropriately long time, his eyes still not meeting hers. "I had a lot to drink that day."

She didn't believe him of course. A Bass never drank anything stronger than an espresso before five pm and certainly not enough to tarnish that famous self-control that the tabloids touted as being the reason for their 'meteoric' rise from the depths of Brooklyn. Normally she would have rolled her eyes and changed the subject, perhaps even leave Chuck to scout for talent at the fringes of the room; but on any other day Serena would have been right there at his side to remind Blair to be kind.

"You didn't seem drunk."

"Well I was. You can ask anybody." He clenched his jaw, still not looking up from his glass, and Blair let out a small sigh before she reached up to gently cup it in her hand. His eyes shot to hers then, burning with unshed tears, before clenching shut when she kissed the corner of his mouth.

"It's sweet," Blair said honestly as she rubbed her red-brown lip-print off his skin with her thumb, "That you think I'm the type of girl that _doesn't_ like to be slapped around." She poked the point of her chin briefly into the soft flesh of his shoulder. "It makes no difference to _me_ whether you're impotent or not. I shouldn't have said anything, I'm sorry."

"I'm not impotent," Chuck whispered, pulling her in close to his body when she tried to step away, his hands fisted into the gathered skirt of her Eleanor Waldorf Original gold dress until she had no choice but to move towards him. Against him. Until her body touched his in a straight line from their shoulders to their knees, and she could feel the truth of his words. "I just can't…not with Serena. Not with any girl and believe me I've _tried_ Blair. It's always the same until I see you, or smell your perfume, or hear your voice; and then suddenly its like I can't get it down."

"What are you trying to say," Blair asked slowly because she needed it, whatever she thought Chuck meant, to be elaborated so that her heart would stop racing. He couldn't mean what she thought he did; he was in love with Serena. Had been in love with Serena ever since she (and Blair) hatched that elaborate plot with a beehive, honey, and Dan Humphrey's new white Converse.

"I'm saying," Chuck flared his nostrils as he glanced down at her lips, a pained look in his eyes, before looking everywhere and anywhere until he eventually caught his father's stern gaze from across the room. Blair already knew that Bart Bass thought she was an unsuitable friend for his son because her mother told her so during dinner one evening when she was fourteen. "I'm saying that I'm in love with Serena but all I can think about is you." He gulped loudly an absolutely devastated expression on his face. "And I don't even like you most of the time, Blair. What's wrong with me?"

Before Blair could reply with one of the thousand one-word responses that fluttered like butterflies through her mind—lust, stupidity, homosexuality, Erotophobia—he let her go with a sneer of something that would have been distaste had his eyes not stared at her as though she were the only thing worth looking at in the room. "Forget it. I already know what's wrong with me. Dad was right."

"About what?" Blair asked guardedly, her heart beating almost right out of her chest as she waited for Chuck to continue. But all Chuck did was glare at her before walking as fast as possible (and still maintain his dignity in a room full of Bass Industries' shareholders) to his father.

Bart Bass patted his son's back, pulled him in to make room for them both in the conversation, and sidled a scathing look at Blair before asking a waiter to refill Chuck's Scotch. It was love Bass style but as Blair glanced to where her mother mingled in the far reaches of the room blissfully unaware that she even had a daughter much less one she had purposefully invited to the soiree in order to seduce one of her prominent suppliers to reduce his prices, she considered it a thousand times better than any kind of love she had ever received.

-


End file.
